Synthesis, anti-human immunodeficiency virus and anti-hepatitis B virus activities of novel oxaselenolane nucleosides [1]

Journal of Medicinal Chemistry

Volumn 40, Issue 19, 1997, Pages 2991-2993

  Du, Jinfa ^a   Surzhykov, Sergey ^a   Lin, Ju Sheng ^b   Newton, M Gary ^a   Cheng, Yung Chi ^b   Schinazi, Raymond F ^c   Chu, Chung K ^a  

^a UNIVERSITY OF GEORGIA   (United States)

^b YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FLUCYTOSINE; LAMIVUDINE; OXASELENOLANE 5 FLUOROCYTOSINE; OXASELENOLANE DERIVATIVE; PYRIMIDINE NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; DRUG SYNTHESIS; HEPATITIS B; HEPATITIS B VIRUS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; LETTER;

ANTI-HIV AGENTS; ANTIVIRAL AGENTS; CYTOSINE; FLUCYTOSINE; HEPATITIS B VIRUS; HIV; HUMANS; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEOSIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030767796     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9703698     Document Type: Letter

References (22)

1. St. Georgiev, V. New synthetic immunomodulating agents. Trends Pharmacol. Sci. 1988, 9, 446-451.
2. De Maeyer, E.; De Meayer-Guignard, J. In Interferons and other Regulatory Cytokines; Wiley: New York, 1988; Chapter 14.
3. De Maeyer, E.; De Meayer-Guignard, J. In Interferons and other Regulatory Cytokines; Wiley: New York, 1988; Chapter 9.
4. (a) Ling, P. D.; Warren, M. K.; Vogel, S. N. Antagonistic effect of in terferon-γ-induced expression of la antigen in murine macrophages. J. Immunol. 1985, 135, 1857-1863.
5. (b) Inaba, K.; Kitaura, M.; Kato, T.; Wantande, Y. Contrasting effects of α/β and γ-interferons on expression of macrophage Ia antigen. J. Exp. Med. 1986, 163, 1030-1035.
6. Hudkins, R. L.; Diebold, J. L. Synthesis of the staurosporine aglycone lactam regioisomer. Tetrahedron Lett. 1997, 38, 915-919.
7. Hudkins, R. L.; Diebold, J. L.; Marsh, F. D. Synthesis of 2-aryl and 2-vinyl-1H-indoles via palladium catalyzed cross coupling of aryl and vinyl halides with 1-carboxy-2-(tributylstannyl) -indole. J. Org. Chem. 1995, 60, 6218-6220.
8. Katritzky, A. R.; Akutagawa, K. Carbon dioxide: A reagent for the protection of nucleophilic centers and the simultaneous activation of alternative locations to electrophilic attach. Part I. A new method for the 2-substitution of 1-unsubstituted indoles. Tetrahedron Lett. 1985, 26, 5935-5938.
9. Immunofluoresence and Cell Sorting. Current Protocols in Immunology; Coico, R., Ed.; Wiley: New York, 1994; Vol. 1, p 5.0.1.
10. (a) Fertsch, D.; Schoenberg, D. R.; Germain, R. N.; Tou, J. Y. L.; Vogel, S. N. Induction of macrophage Ia antigen expression rIFN-γ and down-regulation by IFNα/β and dexamethasone are mediated by changes in steady state levels of Ia mRNA. J. Immunol. 1987, 139, 244-249.
11. (b) Snyder, D. S.; Beller, D. I.; Unaue, E. R. Prostaglandins modulate macrophage Ia expression. Nature 1982, 229, 163-165.
12. Frohman, E. M.; Vayuvegula, B.; Gupta, S.; Van der Noort, S. Norepinephrine inhibits γ interferon-induced major histocompatibility class II (Ia) antigen expression on cultured astrocytes via β2-adrenergic signal transduction Mechanisms. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 1292-1296.
13. Coutinho, G. C.; Durieu-Trautmann, O.; Strosberg, A. D.; Couraud, P. O. Catecholamines stimulate the IFN-γ-induced class II MHC expression on bovine brain capillary endothelial cells. J. Immunol. 1991, 147, 2525-2529.
14. (a) Todd, I.; Pujol-Borrell, R.; Abdul-Karin, B. A. S.; Hammond, L. J.; Feldman, M.; Bottazzo, G. F. HLA-D subregion expression by thyroid epithelium in autoimmune thyroid diseases and induced in vitro. Clin. Exp. Immunol. 1987, 69, 532-542.
15. (b) Buscema, M.; Todd, I.; Deuss, U.; Hammond, L.; Mirakian, R.; Pujol-Borrell, R.; Bottazzo, G. F. Influence of tumor necrosis factor-α on the modulation by interferon-γ of HLA class II molecules in human thyroid cells and its effect on interferon-γ binding. J. Clin. Endocrinol. Metab. 1989, 69, 433-439.
16. Skjodt, H.; Hughes, D. E.; Dobson, P. R. M.; Russell, R. G. G. Constitutive and inducible expression of HLA class II determinants by human osteroblasts-like cells in vitro. J. Clin. Invest. 1990, 85, 1421-1426.
17. Lin, H.-Y.; Thacore, H. R.; Davis, F. B.; Martino, L. J.; Davis, P. J. Potentiation by thyroxine of interferon-g-induced HLA-DR expression is protein kinase A-and C-dependent J. Interf. Cytok. Res. 1996, 16, 17-24.
18. Politis, A. D.; Vogel, S. N. Pharmacologic evidence for the requirement of protein kinase C in IFN-induced macrophage Fc-g receptor and Ia antigen expression. J. Immunol. 1990, 145, 3788-3795.
19. Pitt, A. M.; Lee, C. High throughput screening protein kinase assays optimized for reaction, binding, and detection totally within a 96-well plate. J. Biomol. Screening 1996, 1, 47-51.
20. (a) Takagi, A.; Mizutani, M. Y.; Tomioka, N.; Itai, A. Inhibition mechanisms of staurosporine and H7 to cAMP-dependent protein kinase through docking study. Chem. Pharm. Bull. 1996, 44, 618-620.
21. (b) Furet, P.; Caravatti, G.; Lydon, N.; Priestle, J. P.; Sowadski, J. M.; Trinks, U.; Traxler, P. Modeling study of protein kinase inhibitors: binding mode of staurosporine and origin of the selectivity of CGP 52411. J. Comput. Aided Mol. Des. 1995, 9, 465-472.
22. Nagy, Z. A.; Vidovic, D. The T cell-antigen presenting cell intervention as a site for immunosuppressive intervention. Annu. Rep. Med. Chem. 1995, 30, 199-208.